JPS61127786A - Oil solubilizer - Google Patents

Oil solubilizer

Info

Publication number
JPS61127786A
JPS61127786A JP24874584A JP24874584A JPS61127786A JP S61127786 A JPS61127786 A JP S61127786A JP 24874584 A JP24874584 A JP 24874584A JP 24874584 A JP24874584 A JP 24874584A JP S61127786 A JPS61127786 A JP S61127786A
Authority
JP
Japan
Prior art keywords
oil
fat
acid
weight
polyhydric alcohol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP24874584A
Other languages
Japanese (ja)
Other versions
JPH0144270B2 (en
Inventor
Koichi Iwanami
岩並 孝一
Masaji Ito
伊藤 正次
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NOF Corp
Original Assignee
Nippon Oil and Fats Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Oil and Fats Co Ltd filed Critical Nippon Oil and Fats Co Ltd
Priority to JP24874584A priority Critical patent/JPS61127786A/en
Publication of JPS61127786A publication Critical patent/JPS61127786A/en
Publication of JPH0144270B2 publication Critical patent/JPH0144270B2/ja
Granted legal-status Critical Current

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  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Edible Oils And Fats (AREA)

Abstract

PURPOSE:An oil solubilizer that contains, as essential components, gallic acid, polyhydric alcohol, emulsifier and oil, thus exerting antioxidative effect on feed and food oil for a long period of time. CONSTITUTION:The objective oil solubilizer contains (A) gallic acid, (B) a polyhydric alcohol, preferably glycerol, sorbitol or propylene glycol, (C) an emulsifier, preferably glycerol fatty acid ester, (D) oil or fat, and, when needed, (E) citric acid and/or L-ascorbic acid. Preferably 50-80pts.wt. of the polyhydric alcohol pase containing 5-25wt%of component A and 0-30wt% of component E are combined with the oil phase containing 5-15wt% of component C.

Description

【発明の詳細な説明】 〔産業上の利用分野〕 本発明は飼料用及び食用油脂に対して酸化防止効果を有
する油脂可溶化物に関する。
DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to an oil and fat solubilized product having an antioxidant effect on feed and edible oils and fats.

本発明の「可溶化」とは、可溶化、ミクロエマルション
化、乳化のすべて包含するものとする。
"Solubilization" in the present invention includes all solubilization, microemulsification, and emulsification.

〔従来の技術〕[Conventional technology]

従来、飼料用酸化防止剤としてエトキシキン(″6−ニ
トキシー1.2−ジヒドq−2,2−,4−トリノチル
キノ/)が主に使用されてきたが、その残留性について
間咀があり、叱責規制(150ppm >の点からも安
全性の高いものが望まれている。また、油脂や煮干をは
じめとして食品に広く用いられている情化防と剤のBH
A(ジプチル−4−ヒドロ0キシ7ニソール)も発ガン
の疑いがあることが取り上げられており、近々に食品へ
の使用が禁止になると思われ、関連業界ではすでに使用
自粛の状態にある。これらエトキシキン、BHAとも工
業的に合成されているものであり、世相である天然物指
向に反するものである。このよ5な状況の中で天然物を
使用した安全かつ強力な酸化防止剤が求められていた。
Traditionally, ethoxyquin (6-nitoxy1,2-dihydroq-2,2-,4-trinotylquino/) has been mainly used as an antioxidant for feed, but there has been some controversy regarding its residual properties, and it has been criticized. A product with high safety is desired in terms of regulations (>150 ppm).In addition, BH, an anti-inflammatory agent widely used in foods such as fats and oils and dried sardines, is desired.
A (diptyl-4-hydroxy-7-nisole) has also been reported to be suspected of causing cancer, and its use in food products is expected to be banned in the near future, and related industries are already refraining from using it. Both ethoxyquin and BHA are industrially synthesized, which is contrary to the social trend toward natural products. Under these circumstances, there was a need for safe and powerful antioxidants made from natural products.

〔発明が解決しようとする問題点〕[Problem that the invention seeks to solve]

天然物由来の酸化防止剤として、植物の成分であるタン
ニン酸を加水分解して得られる没食子酸が強い情化防と
効果を有することが知られているが、これは油脂に離溶
性であり300 ppm程腿しかf!消せずしかも加熱
を必要とし、かなりの時間と労力を要し、さらに2価の
鉄イオンと接触することにより青色〜黒色に着色すると
いう欠点があった。
As a natural antioxidant, gallic acid obtained by hydrolyzing tannic acid, a plant component, is known to have strong antioxidant effects, but it is soluble in fats and oils. About 300 ppm only in the thighs! It cannot be erased, requires heating, requires considerable time and effort, and has the disadvantage that it is colored blue to black when it comes into contact with divalent iron ions.

〔間頃点を輯決するための手段〕[Means for deciding between points]

本発明考は、没食子酸が食品衛生上安全な物質であり、
また強い酸化防止効果を有すること忙着防止作用の相乗
効果を引き出し、2価の鉄イオンとの着色も防止できる
という知見を得、エトキシキン、BHAと同等、もしく
はそれよりも強力な酸化防止剤の開発に成功した。
The idea of the present invention is that gallic acid is a food hygienically safe substance;
In addition, we have found that it has a strong antioxidant effect, brings out the synergistic effect of the anti-bust effect, and can also prevent coloring with divalent iron ions. The development was successful.

すなわち、本発明は、没食子酸、多価アルコール、乳化
剤および油脂からなり、必要によりクエン酸および/又
はL−7スコルビン酸を配合してなる酸化防止効果を有
する油脂可溶化物を提供するものである。
That is, the present invention provides a solubilized fat and oil having an antioxidant effect, which is composed of gallic acid, a polyhydric alcohol, an emulsifier, and a fat, and optionally contains citric acid and/or L-7 scorbic acid. be.

本発明の油脂可溶化物は、没食子酸を5〜25重−1:
%、クエン酸および/又はL−7スフルビン酸を0〜3
0重量%含む多価アルコール相50〜80重量部と乳化
剤を5〜15重埼チ含む油脂相20〜50重貴部とから
なる配合割合のものが好ましい。
The fat and oil solubilized product of the present invention contains gallic acid at 5 to 25 weight-1:
%, citric acid and/or L-7 sfulvic acid from 0 to 3
A preferred blending ratio is 50 to 80 parts by weight of a polyhydric alcohol phase containing 0% by weight and 20 to 50 parts by weight of an oil phase containing 5 to 15 parts by weight of an emulsifier.

本発明に用いる没食子酸は通常の市販品が使用可能であ
り、その配合量が上記5重i%未満では所定の酸化防と
効果が得られず、25重i%を越えると油脂への可溶化
が困雌である。
As the gallic acid used in the present invention, ordinary commercially available products can be used. If the amount is less than 5% by weight, the desired antioxidant effect cannot be obtained, and if it exceeds 25% by weight, it may cause damage to fats and oils. It is difficult to dissolve.

本発明に用いる多価アルコールは、水酸基を2ヶ以上有
するアルコールであり、没食子酸を可溶化するため粘度
が低いものが好ましく、例えばプロピレングリコール、
グリセリン、ソルビトールなどが使用できる。
The polyhydric alcohol used in the present invention is an alcohol having two or more hydroxyl groups, and preferably has a low viscosity in order to solubilize gallic acid, such as propylene glycol,
Glycerin, sorbitol, etc. can be used.

セリン脂肪酸エステルなどがあるが、特にポリグリセリ
ン脂肪酸エステルが好ましい。ポリクリセリン詣11h
酸1ステルは重合y2〜122〜12重グリセリンと炭
素数10〜2oの脂肪酸とのエステル化物であり、その
HLBが1〜7のものが使エステルが好ましい。
Among them, polyglycerin fatty acid esters are particularly preferred. Polycrycerin pilgrimage 11h
The acid 1 ester is an esterified product of polymerized y2-122-12 double glycerin and a fatty acid having 10 to 2 carbon atoms, and the ester having an HLB of 1 to 7 is preferably used.

本発明に甲いる油脂は、一般の・天然咲油脂がすべて使
用できるが、良好な油脂可溶化物を得るためKは液体油
が好ましく、その例として大豆油、ナタネ油、ひまわり
油、綿実油などがある。
As the fats and oils used in the present invention, all general and natural blooming oils can be used, but in order to obtain a good solubilized fat, K is preferably a liquid oil, examples of which include soybean oil, rapeseed oil, sunflower oil, cottonseed oil, etc. There is.

本発明の油脂可溶化物は、前記の所定の配合量の範囲が
好ましく、この範囲を外れると優れた酸化防止効果を有
する良好な油脂可溶化物が得られない。
The fat and oil solubilized product of the present invention preferably has a blending amount within the above-mentioned predetermined range, and if it deviates from this range, a good fat and oil solubilized product having an excellent antioxidant effect cannot be obtained.

本発明の油脂可溶化物を得るには、所定の配合量の多価
アルコール相と油脂相とを良く1合し、ホモミキサーや
ホモゲナイザー等の通常の乳化装置を用いて可溶化すれ
ばよい。
In order to obtain the fat-and-oil solubilized product of the present invention, a predetermined amount of the polyhydric alcohol phase and the fat-and-oil phase may be thoroughly combined and solubilized using a common emulsifying device such as a homomixer or a homogenizer.

〔発明の効果〕〔Effect of the invention〕

本発明の酸化防止効果を有する油脂可溶化物は食品衛生
上安全な没食子酸を容易に油脂に可溶化することができ
る。
The solubilized fat and oil having an antioxidant effect of the present invention can easily solubilize gallic acid, which is safe from a food hygiene perspective, in fat and oil.

本発明品を飼料用油脂に添加することにより、調料の劣
化を抑えることができ、また、マーガリン、ショートニ
ング及びフライングオイル等ノ一般食用油脂の酸化防止
剤として広(使用することができる。
By adding the product of the present invention to feed fats and oils, deterioration of the preparation can be suppressed, and it can also be widely used as an antioxidant for general edible fats and oils such as margarine, shortening, and flying oil.

〔実施例〕〔Example〕

実開1 グリセリン 125yに没食子酸 25yさらビン酸を
溶解したものと、ポリグリセリン脂肪酸エステル(@合
すシル−ト、重合度6)6どを溶解したナタネ白絞油 
50yとをホモ2キサーを用いて乳化し、/I61〜9
の油脂可溶化物を得た。
Practical development 1 White rapeseed oil prepared by dissolving 125y of glycerin, 25y of gallic acid, and 25y of benic acid, and 6 of polyglycerin fatty acid ester (@combined silt, degree of polymerization 6).
50y and emulsified using homo2xer, /I61-9
An oil and fat solubilized product was obtained.

その酸化防と効果なA、O,M、(Active Ox
ygenMethod )  により測定した。結果を
表1に示す。
Its antioxidant and effective A, O, M, (Active Ox
ygenMethod). The results are shown in Table 1.

定した。Established.

meクエン1、L−7スコルビン酸の添加量はグリセリ
ンに対する重量%である。
The amount of mecitric acid 1, L-7 scorbic acid added is % by weight based on glycerin.

表1の結果からも明らかなように、本発明の酸化防止効
果を有する油脂可溶化物を添加した精製豚脂は明らかに
酸化が抑えられており、BHAと比較してもすぐれた酸
化防止効果があることがわかる。クエン酸やL−アスコ
ルビン酸の添加による相剰効果は明らかである。
As is clear from the results in Table 1, oxidation is clearly suppressed in the purified lard to which the oil and fat solubilized product having an antioxidant effect of the present invention is added, and it has an excellent antioxidant effect compared to BHA. It turns out that there is. The additive effect of adding citric acid and L-ascorbic acid is clear.

なお、上記の油脂可溶化物を添加した各試料油について
、塩化第2S水溶液による着色試験を行ない、目視判定
を行なったところ、41がかすかに着色したが、他はす
べて着色は見られなかった。
In addition, each sample oil to which the above-mentioned oil and fat solubilized substances were added was subjected to a coloring test using aqueous chloride 2S solution, and visual judgment was performed, and 41 was slightly colored, but no coloring was observed in all the others. .

実施例2 70%含(のソルビトール100yに没食子酸20yと
クエン酸5yを溶解したものと、ショ糖脂肪酸エステル
(HLB3 )4yおよびグリセリン脂肪酸エステル(
HLB4)37を溶解したナタネ白絞油80yとをホモ
ミキサーを用いて乳化した。実施例1と同様の方法によ
り酸化防と効果をA、O,M、により測定したところ、
71時間であった。
Example 2 A solution of 20 y of gallic acid and 5 y of citric acid dissolved in 100 y of sorbitol (containing 70%), 4 y of sucrose fatty acid ester (HLB3) and 4 y of glycerin fatty acid ester (
80 y of rapeseed white oil in which HLB4)37 was dissolved was emulsified using a homomixer. When the antioxidant effect and effectiveness of A, O, and M were measured by the same method as in Example 1,
It was 71 hours.

実施例3 プロピレングリフール 100Fに没食子酸15y、ク
エン酸 5ノを溶解したものと、ポリグリセリン脂肪酸
エステル(重合度4;HLB6)5yを溶解した大豆白
絞油 40yにホモミキサーを用いて乳化した。実施例
1と同様の方法により酸化防止効果をA、O,M、によ
り測定したところ、67時間であった。
Example 3 15 y of gallic acid and 5 y of citric acid were dissolved in propylene glyfur 100F, and 40 y of white soybean oil in which 5 y of polyglycerin fatty acid ester (degree of polymerization: 4; HLB 6) was dissolved were emulsified using a homomixer. . The antioxidant effect of A, O, and M was measured in the same manner as in Example 1 and was found to be 67 hours.

実施例4 60Cに加温した飼料用牛脂にエトキシキン5チ(対グ
リセリン比)を溶解したグリセリン相60重量部をポリ
グリセリン脂肪酸エステル(実施例1と同じ)5チを含
むナタネ白絞油相4o重量部にホモミキサーで乳化した
もの〕を没食子酸の純分0.02重毫チおよび0.05
重量%添加したサンプルを調製した。各試料油及び比較
品として無添加の飼料用牛脂キれぞれ10yを200*
/の共栓つき三角フラスコに採取し、60tZ’の恒温
槽(暗所)釦装置し、1チ月、2チ月、3チ月後の過酸
化物価(p、o、v )を測定した。結果を表2に示す
Example 4 60 parts by weight of a glycerin phase obtained by dissolving 5 parts of ethoxyquin (relative to glycerin) in beef tallow for feed heated to 60C and 4 parts of a rapeseed oil phase containing 5 parts of polyglycerin fatty acid ester (same as Example 1) emulsified by weight part with a homomixer] and the purity of gallic acid was 0.02 kg and 0.05 g.
Samples were prepared with % wt. Additive-free feed-grade beef tallow (10y) to 200* for each sample oil and comparison product
The samples were collected in an Erlenmeyer flask with a stopper, placed in a 60 tZ' constant temperature bath (in the dark), and measured for peroxide values (p, o, v) after 1 month, 2 months, and 3 months. . The results are shown in Table 2.

表  2 表2に示したように、本発明の油脂可溶化物を添加した
飼料用牛脂は、エトキシキンと比較しても、長期保存に
よる過酸化物価の上昇を抑えることができ、極めて安定
化されており、本発明品の酸化防上能がすぐれているこ
とがわかる。
Table 2 As shown in Table 2, the beef tallow for feed to which the oil and fat solubilized product of the present invention has been added can suppress the increase in peroxide value due to long-term storage and is extremely stable, even compared to ethoxyquin. It can be seen that the product of the present invention has excellent antioxidant ability.

特許出願人  日本油脂株式会社 手続補正書(自発) 昭1060年2月26日 特許庁長官 志 賀   学 殿 (特許庁審査官          殿)1、事件の表
示 昭和59年特許願第 248745  号2 発明の名
称 油脂可溶化物 λ 補正をする者 事件との関係  特許出願人 東京都千代田区有楽町1丁目lO番1号東 補正の対象 明細書の発明の詳細な説明の欄 改める。
Patent applicant Nippon Oil & Fats Co., Ltd. Procedural amendment (voluntary) February 26, 1060 Commissioner of the Patent Office Mr. Manabu Shiga (Examiner of the Patent Office) 1 Indication of the case 1982 Patent Application No. 248745 2 Invention Name: Fat and oil solubilized product λ Relationship with the case of the person making the amendment Patent applicant: No. 1-1 Higashi, Yurakucho, 1-chome, Chiyoda-ku, Tokyo Revise the detailed description of the invention in the specification to be amended.

Claims (1)

【特許請求の範囲】 1)没食子酸、多価アルコール、乳化剤および油脂から
なり、必要によりクエン酸および/又はL−アスコルビ
ン酸を配合してなる酸化防止効果を有する油脂可溶化物
。 2)没食子酸を5〜25重量%、クエン酸および/又は
L−アスコルビン酸を0〜30重量%含む多価アルコー
ル相50〜80重量部と乳化剤を5〜15重量%含む油
脂相20〜50重量部とからなる特許請求の範囲第1項
記載の油脂可溶化物。 3)多価アルコールがグリセリン、ソルビトールまたは
プロピレングリコールである特許請求の範囲第1項また
は第2項記載の油脂可溶化物。 4)乳化剤がポリグリセリン脂肪酸エステルである特許
請求の範囲第1項〜第3項のいずれかに記載の油脂可溶
化物。
[Scope of Claims] 1) A solubilized fat and oil having an antioxidant effect, which is composed of gallic acid, a polyhydric alcohol, an emulsifier, and a fat and oil, and optionally contains citric acid and/or L-ascorbic acid. 2) 50 to 80 parts by weight of a polyhydric alcohol phase containing 5 to 25% by weight of gallic acid, 0 to 30% by weight of citric acid and/or L-ascorbic acid, and 20 to 50 parts by weight of an oil phase containing 5 to 15% by weight of an emulsifier. The oil and fat solubilized product according to claim 1, comprising parts by weight. 3) The oil and fat solubilized product according to claim 1 or 2, wherein the polyhydric alcohol is glycerin, sorbitol, or propylene glycol. 4) The oil and fat solubilized product according to any one of claims 1 to 3, wherein the emulsifier is a polyglycerin fatty acid ester.
JP24874584A 1984-11-27 1984-11-27 Oil solubilizer Granted JPS61127786A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP24874584A JPS61127786A (en) 1984-11-27 1984-11-27 Oil solubilizer

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP24874584A JPS61127786A (en) 1984-11-27 1984-11-27 Oil solubilizer

Publications (2)

Publication Number Publication Date
JPS61127786A true JPS61127786A (en) 1986-06-16
JPH0144270B2 JPH0144270B2 (en) 1989-09-26

Family

ID=17182732

Family Applications (1)

Application Number Title Priority Date Filing Date
JP24874584A Granted JPS61127786A (en) 1984-11-27 1984-11-27 Oil solubilizer

Country Status (1)

Country Link
JP (1) JPS61127786A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62153385A (en) * 1985-12-27 1987-07-08 Riken Vitamin Co Ltd Antioxidant
JPH01304872A (en) * 1988-05-31 1989-12-08 Nippon Oil & Fats Co Ltd Bacteriostatic agent
JPH03197595A (en) * 1989-02-01 1991-08-28 Korea Food Dev Research Inst Method for preventing oxidation of oil or fat
JPH044863A (en) * 1990-04-19 1992-01-09 Ezaki Glico Co Ltd Method for improving preservability of food using fat or oil
WO1992000019A1 (en) 1990-06-26 1992-01-09 Kalamazoo Holdings, Inc. Activated ascorbic acid antioxidant compositions and carotenoids, fats, and foods stabilized therewith
JPH09208986A (en) * 1996-02-02 1997-08-12 Okatsune Shoji Kk Antioxidizing agent preparation
US6538019B1 (en) * 2000-03-29 2003-03-25 Japan As Represented By Director Of National Food Research Institute, Ministry Of Agriculture, Forestry And Fisheries Functional emulsions
JP2007503499A (en) * 2003-08-22 2007-02-22 オイ ベガオイルズ リミテッド Antioxidants and their use
US20120215016A1 (en) * 2003-04-04 2012-08-23 Kemin Industries, Inc. Lipid-Soluble Formulations Containing Mixtures of Antioxidants
JP2013172671A (en) * 2012-02-24 2013-09-05 Kao Corp Oil-and-fat composition
WO2019187242A1 (en) * 2018-03-28 2019-10-03 不二製油グループ本社株式会社 Fat composition
WO2024024928A1 (en) * 2022-07-29 2024-02-01 辻製油株式会社 Composition for suppressing discoloration due to heating

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018190203A1 (en) * 2017-04-11 2018-10-18 富士フイルム株式会社 Antioxidant dispersion

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5518436A (en) * 1978-07-28 1980-02-08 Tokyo Tanabe Co Ltd Fat-soluble antioxidant composition and its preparation
JPS5774384A (en) * 1980-10-27 1982-05-10 Nippon Kagaku Shiryo Kk Antioxidant compsition
JPS5971387A (en) * 1982-10-18 1984-04-23 Nippon Oil & Fats Co Ltd Antioxidant pharmaceutical for coating

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5518436A (en) * 1978-07-28 1980-02-08 Tokyo Tanabe Co Ltd Fat-soluble antioxidant composition and its preparation
JPS5774384A (en) * 1980-10-27 1982-05-10 Nippon Kagaku Shiryo Kk Antioxidant compsition
JPS5971387A (en) * 1982-10-18 1984-04-23 Nippon Oil & Fats Co Ltd Antioxidant pharmaceutical for coating

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0464638B2 (en) * 1985-12-27 1992-10-15 Riken Vitamin Co
JPS62153385A (en) * 1985-12-27 1987-07-08 Riken Vitamin Co Ltd Antioxidant
JPH01304872A (en) * 1988-05-31 1989-12-08 Nippon Oil & Fats Co Ltd Bacteriostatic agent
JPH0565150B2 (en) * 1988-05-31 1993-09-17 Nippon Oils & Fats Co Ltd
JPH03197595A (en) * 1989-02-01 1991-08-28 Korea Food Dev Research Inst Method for preventing oxidation of oil or fat
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JPH09208986A (en) * 1996-02-02 1997-08-12 Okatsune Shoji Kk Antioxidizing agent preparation
US6538019B1 (en) * 2000-03-29 2003-03-25 Japan As Represented By Director Of National Food Research Institute, Ministry Of Agriculture, Forestry And Fisheries Functional emulsions
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US9725675B2 (en) * 2003-04-04 2017-08-08 Kemin Industries, Inc. Lipid-soluble formulations containing mixtures of antioxidants
JP2007503499A (en) * 2003-08-22 2007-02-22 オイ ベガオイルズ リミテッド Antioxidants and their use
JP2013172671A (en) * 2012-02-24 2013-09-05 Kao Corp Oil-and-fat composition
WO2019187242A1 (en) * 2018-03-28 2019-10-03 不二製油グループ本社株式会社 Fat composition
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